Journal of Organic Chemistry, volume 80, issue 24, pages 12212-12223
Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly
Ekaterina M Budynina
1, 2
,
Olga Ivanova
1, 2
,
Alexey O Chagarovskiy
1, 2
,
Yuri Grishin
1
,
Igor V Trushkov
1, 2
,
1
Department
of Chemistry, M.V. Lomonosov Moscow State University, Leninskie
Gory 1-3, Moscow 119991, Russia
|
Publication type: Journal Article
Publication date: 2015-12-01
Journal:
Journal of Organic Chemistry
Q2
Q1
SJR: 0.724
CiteScore: 6.2
Impact factor: 3.3
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
We report a new simple method to access highly substituted cyclopentanes via Lewis acid-initiated formal [3 + 2]-cycloaddition of donor-acceptor cyclopropanes to 1,3-dienes. This process displays exceptional chemo- and regioselectivity as well as high diastereoselectivity, allowing for the synthesis of functionalized cyclopentanes and bicyclic cyclopentane-based structures in moderate to high yields. Moreover, one-pot synthesis of biologically relevant cyclopentafuranones, based on reaction of donor-acceptor cyclopropanes with dienes, has been developed.
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GOST
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Budynina E. M. et al. Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly // Journal of Organic Chemistry. 2015. Vol. 80. No. 24. pp. 12212-12223.
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Budynina E. M., Ivanova O., Chagarovskiy A. O., Grishin Y., Trushkov I. V., Melnikov M. Y. Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly // Journal of Organic Chemistry. 2015. Vol. 80. No. 24. pp. 12212-12223.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.5b02146
UR - https://doi.org/10.1021/acs.joc.5b02146
TI - Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly
T2 - Journal of Organic Chemistry
AU - Budynina, Ekaterina M
AU - Ivanova, Olga
AU - Chagarovskiy, Alexey O
AU - Grishin, Yuri
AU - Trushkov, Igor V
AU - Melnikov, Mikhail Y.
PY - 2015
DA - 2015/12/01
PB - American Chemical Society (ACS)
SP - 12212-12223
IS - 24
VL - 80
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2015_Budynina,
author = {Ekaterina M Budynina and Olga Ivanova and Alexey O Chagarovskiy and Yuri Grishin and Igor V Trushkov and Mikhail Y. Melnikov},
title = {Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly},
journal = {Journal of Organic Chemistry},
year = {2015},
volume = {80},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.joc.5b02146},
number = {24},
pages = {12212--12223},
doi = {10.1021/acs.joc.5b02146}
}
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Budynina, Ekaterina M., et al. “Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to 1,3-Dienes: Cyclopentane Assembly.” Journal of Organic Chemistry, vol. 80, no. 24, Dec. 2015, pp. 12212-12223. https://doi.org/10.1021/acs.joc.5b02146.